Sodium hydride → HCID 68411742, compound

HRID 1887756Notes

Reaction equation

HRID 1887756 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH:8]([NH:13][C:14](=[O:34])[CH:15]([NH:20][C:21](=[O:33])[C:22]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:24])[CH3:23])[CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:7]2.Br.Br[CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=1.[H-].[Na+]>CN(C=O)C>[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=1)[C:9](=[O:12])[CH:8]([NH:13][C:14](=[O:34])[C@H:15]([NH:20][C:21](=[O:33])[C:22]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:23])[CH3:24])[CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:7]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27347202-(Bromomethyl)pyridine hydrobromideHCID 68412613HCID 68412613, compound

Product 1

HCID 68411742HCID 68411742, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyl 1-(1-(8-amino-2-oxo-1,2,3,4-tetrahydroquinolin-3-ylamino)-4-methyl-1-oxopentan-2-ylamino)-2-methyl-1-oxopropan-2-ylcarbamate (1.04 g) and 2-(bromomethyl)pyridine hydrobromide (553 mg) were sequentially added to N,N-dimethylformaldehyde (7.5 mL), and sodium hydride (174 mg) was added in two portions to the mixture under cooling on ice, followed by stirring for two hours. The resultant mixture was extracted with ethyl acetate and water, and the aqueous layer was further extracted with ethyl acetate. The organic layers were combined, and the combined organic layer was dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the thus-recovered residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:2), whereby the title compound (393 mg) was yielded.

Workup

  1. additionwas added in two portions to the mixture
  2. temperatureunder cooling on ice
  3. extractionThe resultant mixture was extracted with ethyl acetate and water
  4. extractionthe aqueous layer was further extracted with ethyl acetate
  5. dry with materialthe combined organic layer was dried over sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe thus-recovered residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:2), whereby the title compound (393 mg)
  8. customwas yielded

Sources & evidence

ORD record
ord-412446c3dc5f487aa576113a89166979
Source dataset
uspto-grants-2013_08
Patent number
US08501772B2

Reaction notes

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